Dicyclo­hexyl­ammonium hydrogen phenyl­phospho­nate

Tidiane Diop; Libasse Diop; Thierry Maris; Helen Stoeckli-Evans

doi:10.1107/S160053681201553X

. 2012 Apr 18;68(Pt 5):o1432. doi: 10.1107/S160053681201553X

Dicyclohexylammonium hydrogen phenylphosphonate

Tidiane Diop ^a,^*, Libasse Diop ^a, Thierry Maris ^b, Helen Stoeckli-Evans ^c

PMCID: PMC3344552 PMID: 22590314

Abstract

In the title salt, [(C₆H₁₁)₂NH₂]⁺·[C₆H₅PO₂(OH)]⁻, the anion is monodeprotonated and acts as both a hydrogen-bond donor and acceptor. The anions are linked by pairs of O—H⋯O interactions, forming inversion dimers with R ₂ ²(8) ring motifs. These dimers are bridged by two dicyclohexylaminium cations via pairs of N—H⋯O hydrogen bonds, giving R ₄ ⁴(12) ring motifs, forming chains propagating along [010]. The chains are bridged by C—H⋯O interactions, forming a two-dimensional network lying parallel to (101).

Related literature

For the crystal structure of phenylphosphonic acid, see: Weakley (1976 ▶). For the crystal structure of anilinium phenylphosphonate, see: Mahmoudkhani & Langer (2002 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₂H₂₄N⁺·C₆H₆O₃P⁻
M _r = 339.40
Monoclinic,
a = 13.3212 (4) Å
b = 8.9093 (3) Å
c = 16.0670 (5) Å
β = 104.385 (1)°
V = 1847.09 (10) Å³
Z = 4
Cu Kα radiation
μ = 1.43 mm⁻¹
T = 150 K
0.16 × 0.12 × 0.08 mm

Data collection

Bruker Microstar diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.749, T _max = 0.892
21802 measured reflections
3456 independent reflections
3221 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.098
S = 1.08
3456 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681201553X/hb6721sup1.cif

e-68-o1432-sup1.cif^{(28.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201553X/hb6721Isup2.hkl

e-68-o1432-Isup2.hkl^{(169.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681201553X/hb6721Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O1ⁱ	0.84	1.75	2.5920 (13)	175
N1—H1A⋯O1	0.92	1.86	2.7520 (14)	161
N1—H1B⋯O2ⁱⁱ	0.92	1.81	2.6897 (15)	159
C18—H18A⋯O3ⁱⁱⁱ	0.99	2.52	3.3019 (16)	136
C18—H18B⋯O2ⁱⁱ	0.99	2.52	3.2693 (16)	133

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

supplementary crystallographic information

Comment

In the title salt (Fig. 1), the hydrogen phenylphosphonate anion is unequivocally tetrahedral, with three oxygen atoms and a phenyl group; O2—P1—O1 116.59 (5)°, O3—P1—C1 104.45 (5)°. The P—O distances are different [1.4870 (10) Å for P═O, 1.5134 (9) Å for P-O^-, and 1.574 (3) Å for bond P-O(H)]. This is similar to the situation in the crystal structure of the parent phenylphosphonic acid PhPO₃H₂ (Weakley, 1976), with bond distances of 1.496 Å for P═O and 1.545 Å for P—O(H).

In the crystal, the anions are linked by a pair of O-H···O hydrogen bonds to form inversion dimers with a ring motif of R²₂(8) (Bernstein et al., 1995; Table 1 and Fig. 2). These dimers are linked by two dicyclohexylaminium cations, via pairs of N-H···O hydrogen bonds forming a ring motif of R⁴₄(12), to form chains propagating along [010], as shown in Table 1 and Fig. 2. A similar chain arrangement has been observed in the crystal structure of anilinium phenylphosphonate (Mahmoudkhani & Langer, 2002). In the title compound the chains are linked by C-H···O interactions to form a two-dimensional network that lies parallel to (101); see Table 1 and Fig. 2.

Experimental

When dicyclohexylamine was allowed to react with phenylphosphonic acid in an equimolar ratio (1:1) in water, a precipitate was obtained and filtered [Yield: 83%; M.p: 448 K]. The filtrate was allowed to evaporate at 333 K, giving colourless block-like crystals of the title compound.